2-Cyclopropen-1-one, 2,3-diphenyl-

• Formula: C₁₅H₁₀O
• Molecular weight: 206.2393
• IUPAC Standard InChI: InChI=1S/C15H10O/c16-15-13(11-7-3-1-4-8-11)14(15)12-9-5-2-6-10-12/h1-10H Copy

  
• IUPAC Standard InChIKey: HCIBTBXNLVOFER-UHFFFAOYSA-N Copy
• CAS Registry Number: 886-38-4
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: Cyclopropenone, diphenyl-; Cyclopropenone, 2,3-diphenyl-; Diphenylcyclopropenone; 2,3-Diphenylcyclopropenone; 2,3-Diphenyl-2-cyclopropen-1-one; Diphencyprone; DPC; 2,3-diphenylcycloprop-2-en-1-one
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
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Gas phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Condensed phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of sublimation

Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

=  + 

By formula: C₁₅H₁₀O = C₁₄H₁₀ + CO

Gas phase ion energetics data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Steele, Gammon, et al., 1985
Steele, W.V.; Gammon, B.E.; Smith, N.K.; Chickos, J.S.; Greenberg, A.; Liebman, J.F., The standard molar enthalpy of formation of 2,3-diphenylcycloprop-2-en-1-one, J. Chem. Thermodyn., 1985, 17, 505-511. [all data]

Grabowski, Simon, et al., 1984
Grabowski, J.J.; Simon, J.D.; Peters, K.S., Heat of formation of diphenylcyclopropenone by photoacoustic calorimetry, J. Am. Chem. Soc., 1984, 106, 4615-4616. [all data]

Hopkins, Bostwick, et al., 1976
Hopkins, H.P., Jr.; Bostwick, D.; Alexander, C.J., The thermochemistry of diphenylcyclopropenone. Strain vs. delocalization energy, J. Am. Chem. Soc., 1976, 98, 1355-1357. [all data]

Greenberg, Tomkins, et al., 1983
Greenberg, A.; Tomkins, R.P.T.; Dobrovolny, M.; Liebman, J.F., The strain energy of diphenylcyclopropenone: A reexamination, J. Am. Chem. Soc., 1983, 105, 6855-6858. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Hung and Grabowski, 1992
Hung, R.R.; Grabowski, J.J., Enthalpy measurements in organic solvents by photoacoustic calorimetry: a solution to the reaction volume problem, J. Am. Chem. Soc., 1992, 114, 351-353. [all data]

Herman and Goodman, 1989
Herman, M.S.; Goodman, J.L., Determination of the enthalpy and reaction volume changes of organic photoreactions using photoacoustic calorimetry, J. Am. Chem. Soc., 1989, 111, 1849-1854. [all data]

Muller, Schweig, et al., 1978
Muller, C.; Schweig, A.; Vermeer, H., Photoelectron spectra of 1,2-diphenylcyclopropene, 2,3-diphenylcyclopropenone, 2,3-diphenylcyclopropenethione, 2,3-diphenylthiirene and 1-oxide; cis-stilbene, An experimental verification of conjugative inductive interactions, J. Am. Chem. Soc., 1978, 100, 8056. [all data]

Dehmlow, Dehmlow, et al., 1977
Dehmlow, E.V.; Dehmlow, S.S.; Marschner, F., Chemische und photoelektronenspektroskopische Eigenschaften von cyclopropylsubstituierten Cyclopropenonen, Chem. Ber., 1977, 110, 154. [all data]

Notes

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• Symbols used in this document:
  

  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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